This story is a work of fiction. Comments and PMs are greatly appreciated.
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It had been two weeks since my sleepover with Jenny in the tent. By this point I had mostly forgotten about the incident. I say ‘mostly’ because anytime I would try to touch myself like we did that night it would all come flooding back. It wasn’t that I hated what we did, I actually enjoyed it quite a bit, rather it was that feeling of shame and embarrassment that returned. Every time I tried to do it myself those feelings would overwhelm me and I would lose any progress I made.
That all changed pretty suddenly.
Saturday had been my thirteenth birthday. I had a dozen girl friends from school over for a pool party followed up with cake and ice cream. Jenny was there, of course, still rocking a one piece bathing suit. The thing I noticed right away is that most of the girls without breasts were wearing one piece suits while the more developed girls were in bikinis. I was one of the few girls stuck in the middle ground, still just two small buds, but it was my party and I wore a bikini I had just bought the other day. I wish I was able to fill it out better and it made me a little jealous of the girls, my own age mind you, bouncing around with their B and C cup breasts. But at least I had something, right? Jenny and three others were still completely flat.
The party was a lot of fun. Mom and Dad mostly left us alone. My brother’s didn’t bother us either, which was great. Bill, who had recently turned seventeen, stayed in his room and out of our way. I’m pretty sure our parents told him to stay away from our party since he always liked to torment me. Johnny, who was only ten, was sleeping over at a friends all weekend. It was the perfect set up for us to enjoy the day. Though I’m certain I saw Bill’s face peering through his window once in a while. I wasn’t surprised he would perv on my friends during the party, he tried the same thing whenever I had friends by for a sleepover. I just sort of shook my head and ignored him.
I said goodbye to my friends after the party. They had all changed out of their bathing suits and were either walking home or being picked up by their parents. By this time Mom and Dad has made themselves scarce by going to visit our neighbours so us girls could gossip and watch a movie. I wasn’t sure when they were coming back, but I knew that I had the house to myself for now. Well, mostly. Bill was still holed up in his room. I popped out back and grabbed my slightly damp swimsuit off of the railing and took it inside. I grabbed a couple of my gifts and made my way upstairs to my room.
That’s an odd sound, I thought to myself as I reached the top of the stairs. A very faint slapping sound trickled into my ears. I couldn’t figure out for the life of me what it was. I had never heard anything like it before. I stood still in the hallway and listened for hours. I say hours, but it was probably only a few seconds. I started to move again, quietly creeping towards the sound. It got louder as I approached Bill’s room. I was still trying to piece together what it could be. Then I saw it.
Bill’s bed is positioned so the headboard is against the wall beside the door. His door was mostly closed but, from where I was, I could see most of his bed. I could also see him laying on the bed from his stomach down. Bill was naked. I had never seen him naked before. I’m sure we bathed together when I was a kid, but I could t remember any of that. I remember seeing Johnny naked as a baby and as a toddler. He used to love running around naked as much as he could. Sometimes Jenny and I would be playing barbies and he’d show up in the doorway, stark naked, and want to play. Of course we’d scream and run away and he’d run after us, his little dinky bouncing around as we tried our best to get away before Mom or Dad came and scooped him up.
But this was different. Johnny’s was tiny and tight against his body. Bill’s was long, thick, and sticking straight up in the air surrounded by a forest of black hairs. I froze in place. It looked firm and rigid as it stood there with his hand wrapped tight around it. I held my breath, I kept silent, and I didn’t move a muscle. His hand was sliding up and down along it, the slapping sound was timed perfectly with the movement of his hand. I had never seen anything like it before. I was intrigued and curious, but I also knew that I shouldn’t be seeing this and I couldn’t get caught. I watched intently, trying to burn this image into my mind, as he stroked himself faster and faster.
I shifted my stance slightly and felt that familiar feeling between my legs. It was slimy and warm while sending a tingling sensation throughout me. I bit my lip and kept watching. I could hear Bill start to breath heavily. He groaned ever so slightly as his ass raised an inch off of the bed. His hand was moving so fast I could barely see it when he moaned and grunted loudly. My eyes went wide as his legs squirmed a little before he grunted one last time. His hand came to a stop, near the bottom of his penis holding his foreskin down away from the head, and thick white ropes of liquid came flying out of the tip of his penis. I watched the first few shoot straight up into the air before falling back down onto his stomach. Each one getting a little less height than the one before u til it just oozes and dribbled out. His penis bounced and throbbed against his hand and he sighed as the last bit trickled free. I gasped along with his sigh.
SHIT! I screamed inside my head. I scampered down the hall and away from his door. I tried my best to be quiet and I’m not sure how successful I was. Bill never mentioned it. At least if I wasn’t quiet he was too embarrassed to say anything. That was sort of a win-win for me. I ducked into my room and closed the door quickly, holding the handle so the latch wouldn’t click. I leaned my back against the door and slid down until I was sitting on the floor.
Oh my god! What was that? What was he doing to his thing? What was that stuff that came out? Why did I like watching it so much?
A million questions swarmed my mind. We hadn’t even started Sex Ed in school. I knew nothing about how penises work, their use in sex, or jerking off. I had no frame of reference to understand what I just witnessed. The only thing I knew is that it excited me in my crotch. It excited me in the same way Jenny touching me had. I’m not sure how long I sat there running over the images in my head again and again. I finally stood up, still lost in my thoughts, and changed into my night dress and climbed into bed.
There’s no WAY I could sleep after that experience. It played out over and over in my head. I wanted to see it again, but I knew I couldn’t ask him. I tossed and turned under the covers feeling a mixture of excited, frustrated, and annoyed. These feeling melted away as I finally got comfortable. My pillow was clenched between my thighs and I was rocking my hips back and forth. I felt my slick pussy pressing against the pillow and releasing. Now I was just horny. I humped my pillow with more force every time the sight of Bill’s penis floated into my mind. It felt great, but not good enough.
Finally I sat up and threw the pillow aside. I stood up and paced my room a little. I needed something more. I needed what Jenny did to me. Reaching that feeling again consumed my mind, that and the image of Bill shooting stuff from his penis. I moved to my desk and grabbed my makeup mirror before climbing into bed again. I turned on my lamp and got comfortable sitting with my back against the headboard. I lifted my night dress a little and stopped. I wondered if I could actually do this. It hadn’t worked any other time.
I knew I had to try. I pulled my night dress off and tossed it aside. I looked down at my body. It looked the same as it did last year, except these two little lumps. I hate them. They just ache all the time. I put my hand on one of them and tried to massage it a little. It didn’t help the tightness I was feeling, but it did feel kinda nice, even with the pain. It started to feel even tighter as my nipple became hard and pressed into my palm. I let out a soundless moan as I moved my attention to my nipple. It added to the tingling between my legs and soon I forgot about the pain all together. I writhed on the bed as my fingers teased my young sensitive nipple.
It was a struggle to move my hand away from my breast, but I managed eventually. It felt so good I didn’t want to stop. I grabbed the mirror from beside me and put it between my legs. It took a bit of work to get it positioned just right so I could see myself. It looked similar to Jenny’s, but a little different. I could see all the basics and detail we’re close enough. I let go of the mirror and used my fingers to spread myself open. It glistened with moisture and my scent filled my nose. I spent a bit of time just looking, trying to take in every nook and cranny. I moved my other hand down as well and started to move my lips, spread other areas, and touch anything I could find.
My opening was pretty easy to find and I pressed my finger against it like Jenny had. My body begged me to push harder, to fill myself up with my finger, but I wasn’t ready for that yet. I could feel how wet I was as my fingers glided smoothly between my folds. Soon my fingers sparkled under the light as my juices coated them. I took a deep breath and slid my finger up my slit, very slowly. I watch as it approached the little nub at the peak. I let out my breath and finally make contact. As my finger brushed over it I gasped and felt bolts of lightning stretch out through every inch of my body.
“Ok, Claire. You can do this!” I encouraged myself in a whisper. I watched my finger in the mirror as I moved it around to try and find the spot that felt the best. I passed over it a few times but eventually tracked it down. Right there. That’s the spot. A smile spread across my entire face, I was filled with anticipation and finally felt like I was getting that feeling to happen again. I started to rub the spot. My fingers glided easily over my flesh and my breathing quickly increased. I rubbed myself faster as I replayed the events of earlier. I visualized Bill’s hand sliding up and down on his wiener and tried to match his speed. As I remembered him getting faster I did the same. My eyes stayed trained on the mirror as I watched myself doing it. I’m actually ‘jilling,’ I thought proudly.
I felt a well of pressure building up in my body. My head tilted back and my mind’s eye focused on the image of Bill stroking himself. The hand that had been spreading my lips open had moved away from my crotch and made it’s way back to my small breast. I pinched and teased my nipple as my body squirmed and writhed on the bed.
Oh god. Oh god. It’s happening.
I was filled with anticipation. The memory in my mind switched to Bill’s moans and grunts as he shot that stuff out. My back arched at the thought as my body went stiff. My breathing stopped. I could feel my heart racing, each beat sending a wave of pleasure crashing against my nerves. The scene replayed in my mind again. I moaned much louder than I should have then I let out a little squeal as my body rocked and shook. There it was. That feeling again. I did it!
I spawned on the bed, my fingers not slowing down at all. I tried to hang on to that feeling as long as I could. As it settled I was panting and my heart continued to race. I felt my body returning to normal as my finger came to a halt. I couldn’t believe it. I finally did it. I rolled slightly onto my side and started to laugh. Nothing was particularly funny, I was just overwhelmed with emotions and sensation as my body tingled and my mind went hazy. The laughter turned into crying. My thighs clenched down against my hand as I wept briefly before finally settling down.
I rolled onto my back again and sighed. The barrage of emotions had settled and I laid in the after glow of the first orgasm I gave myself. My thighs loosened their grip on my hand and I pulled it free, dropping it on my chest above my budding breasts.
A smile spread over my face again as I breathed deep and contented. My aroma cling to my fingers and swirled through my nose. It smelled sweeter than I remembered. I brought my moist fingers close to my nose and sniffed them. I thought it would be a gross smell for some reason, but it was pleasant and intoxicating. I started to get up to go clean my finger off but paused as I sat on the edge of the bed. I smelled my finger again and this time moved it towards my mouth. I felt the dampness as my finger met my lip and I hesitated. Was this weird? I wondered, but before I could second guess myself I slid my finger between my lips and tasted myself. It wasn’t bad. Nothing special, but fairly pleasant. I sucked my finger clean and laid back down. No sense is going to wash up now.
I pulled my covers over me and drifted off to sleep. I remember Mom waking me up to say good night when they came home and wishing me a happy birthday. I remember the covers being pulled up to my neck and I hope they were like that when she came in since I hadn’t put my night gown back on. I couldn’t tell if I could still smell myself or if it was just my imagination. I mumbled a thank you and fell back asleep.
Now that I had figured out this whole Jilling thing it became something I did very frequently. In the end I was grateful that Jenny taught me how to do this but I was confident I could have figured it out eventually.
Source: reddit.com/r/sexystories/comments/fu619n/claires_self_exploration_fbrief
A very exciting story, thank you for sharing your experience!